
Family-friendly holiday rentals in Hampshire County
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Hampshire County
Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.

The Creation Station
Welcome to The Creation Station. I am your host John. The Creation Station was built with love and care by me with my friends and family. Amenities? Update! We just installed an 8 person hot tub! Plus our pool, jacuzzi tub, projector, giant deck and a stage with sound system, drums amps and karaoke input. The most unique amenity though is The Enchanted Forest. A lit trail surrounding the property. Fun for kids of all ages! Please let me know how I can make your stay amazing. See you soon! John

Cider House Cottage
Antique guest cottage on a becountry farm property with acres of fields, ponds, forests and streams, adjoining Quabbin Reservoir domain. Ideal for hikers, bird watchers, and bicyclists, this quiet country retreat offers trails and terrain to explore, only 3 miles away from small historic New England town. Make yourself at home in the comfortably furnished post and beam home with terrace and pond views, adventure in the surroundings, dip in fresh water streams, and relax in the claw foot bathtub

The cozy clubhouse
Take a break and unwind at this peaceful cozy studio apartment with a private deck looking out over the garden and classic New England stone wall. Located on a quiet dead end street in the village of Haydenville. Not far from the local rail trail, hiking trails, and only a 13 minute drive to downtown Northampton. Very close to Look Park and Valley View Farm common wedding venues. A gateway to the Berkshires, with easy drive access to the Tanglewood music venue, Mount Greylock, and Mass MOCA.

Berkshires Cottage by Lake. Year Round Adventures.
THE BERKSHIRES COTTAGE IN THE WOODS BY A SPRING FED LAKE HAS SOMETHING FOR EVERYONE....... SWIM, FISH, KAYAK, HIKE, SKI, JACOBS PILLOW DANCE FESTIVALS, TANGLEWOOD OUTDOOR CONCERTS, GOLF, DINE, SHOP LEE OUTLETS, DINE WITH ENTERTAINMENT, PLAYS, ANTIQUES, FIRE PITS, HANGING IN A HAMMOCK, FLOAT ON CRYSTAL CLEAR WATER, BBQ ON THE DECK, OR JUST DOING NOTHING AT ALL UNPLUG AND RECHARGE. ESCAPE & RELAX. (90 second walk through wooded path to lake) Pets Considered. Approved pet = approved Pet Agreement.

Separate apt, 1 mile from downtown, 1 guest only
This is a private, clean, comfortable apartment with New pillow top mattress for 1 person with separate entrance in our new home. You will have the space to yourself. We are a mile from downtown near the bike path, the mill river, and Smith college. Private bathroom with a shower; kitchen basics: fridge, microwave, toaster, teapot, pour over coffee. Wifi and smart tv. Sunny with central air in the summer warm and cozy in the winter. Walk or ride a bike to town. Weโre located in Village Hill.

Cozy Hilltown Cottage
Enjoy a peaceful stay in this cozy, creative space. Set on 10 acres of gardens and woods, this cottage is perfectly located to explore Western Massachusetts - with places like MASS MoCA, Shelburne Falls, Tanglewood and Northampton all within a 30min to 1 hour drive. Upstairs is a queen bed and full bath, while downstairs features a functional kitchen, work desk, grand windows, and a living space with full sleeper sofa. We live in the main house on property but respect your privacy-see photos!

Just Be Cabin
Small, rustic cabin in the woods behind our home. The cabin has electricity, but no running water. Drinking and cooking water are provided from a hand pumped container. The cabin is a beautiful place to slow down, connect to nature and one's self. If you love to camp, you will love the cabin. It is the perfect locale for a personal retreat. We are happy to arrange a yoga class at our home studio as well. It is like a tree house, where all are welcome to come, simplify life and just be.

Happy Maples!
I am a custom builder and I decided to have some fun building out my own special guest space. Welcome to Happy Maples! The suite is a private 600 sq ft hand crafted studio with private entrance, bath w/shower, large deck w/Adirondack chairs and grill, views of the gardens and 100' from the historic Mill River right behind the house. There is a queen bed and an additional twin memory foam bed available. 12 mins to Northampton, 20 mins to Amherst, Bike trail in back yard. Come for a fun visit!

Mountain Retreat close to Northampton & Amherst!
Come have this mountain top home situated on 150 secluded acres in beautiful historic Williamsburg all to yourselves!! If you want privacy within 10-20 minutes from Northampton, Hadley, and Amherst, then this cabin is perfect. Within walking distance, you will have access to trail systems for either your hiking or biking endeavors. You can stay and enjoy the peaceful nature of our home, sit on the massive deck while you gaze upon breathtaking views of the Pioneer Valley, or venture out.

Tiny House Farm Retreat: Mountain Views, Fire pit
The Tiny House at Milestone Farm is a cozy farm retreat loaded with modern conveniences. Designed as a romantic escape for couples to relax and enjoy the tranquility of the farmlands while viewing the beautiful Holyoke range. Take in the amazing views and watch the many facets of commercial farming during the growing season. Create your own menu using our fully stocked kitchen. Meat and seasonal produce available for purchase in our farmstand. Minutes from the center of Northampton.

Hilltown Studio
Stunning 2nd floor studio (limited kitchenette with easy to prepare Breakfast foods provided) close to Northampton, Smith and the Five Colleges, scenic drive to the Berkshires, one mile to the Snow Farm and just minutes to Valley View Farm. Lovely space & private deck overlooking perennial gardens & wildlife wandering by. Perfect stop when traveling through Western Mass, touring local colleges or a trip to enjoy the music, museums and restaurants in the Pioneer Valley and Berkshires.

AirbytheStream waterfront, private, clean and cozy
Beautiful private camper with outdoor deck on the water. All the creature comforts but half the price. Very private yet 15 minutes to Northampton or Easthampton. Kitchen sink, 2 burner stove, refrigerator, toilet and shower, one queen bed and twin bunk beds, dinette can also turn into a bed. Pots and pans, silverware and cooking utensils are provided. Camper has power and water as well as heat and air conditioning. There is a Blackstone griddle for outdoor cooking.
Popular amenities for Hampshire County family-friendly rentals
Family-friendly home rentals with a hot tub

The View Guest Suite - Amherst

Sweet suite, walk to town tout suite!

Serene South Deerfield Retreat

Hadley Hay House | No Cleaning fees!

Hilltown Cabin Hideaway: A River Runs Through It!

The Farmhouse - Hot tub eclectic farmhouse 3 br

Luxury Glamping, Private, Wood Burning Hot Tub

Long Mountain Suite W/Hot tub
Family- and pet-friendly home rentals

Bright Noho studio suite perfect walk to downtown

Peaceful Cabin in the Woods

Stone n' Sky Lodge

Zachariah House Main St. Ashfield

Swiss Chalet Style Timberframe Home in Berkshires

House Above the Hollow

Tulsi Rose Healing Retreat

Sunny Chalet Nestled in the Woods of Ashfield
Family-friendly home rentals with a pool

Sunset Ridge

Happy Valley getaway

Nestled Inn

Sweet cape near U Mass

NE Historical Mansion-pets and pet lovers welcome

High Field Farm

Enjoy every season the Berkshires have to offer.

1880s bright sun+design in best downtown location
Destinations to explore
- Rentals with a hot tubย Hampshire County
- House rentalsย Hampshire County
- Rentals with outdoor seatingย Hampshire County
- Guest house rentalsย Hampshire County
- Rentals with poolsย Hampshire County
- Rentals with lake accessย Hampshire County
- Rentals with a patioย Hampshire County
- Private suite rentalsย Hampshire County
- Rentals with a washing machine and dryerย Hampshire County
- Rentals with a fireplaceย Hampshire County
- Pet-friendly rentalsย Hampshire County
- Rentals with a firepitย Hampshire County
- Rentals with a kayakย Hampshire County
- Rentals with an EV chargerย Hampshire County
- Smoking-friendly rentalsย Hampshire County
- Bed and breakfastsย Hampshire County
- Rentals with breakfastย Hampshire County
- Flat rentalsย Hampshire County
- Family-friendly rentalsย Massachusetts
- Family-friendly rentalsย United States
- Six Flags New England
- Berkshire East Mountain Resort
- Jiminy Peak Mountain Resort
- Monadnock State Park
- Catamount Mountain Ski Resort
- Butternut Ski Area and Tubing Center
- Mount Snow Ski Resort
- Bash Bish Falls State Park
- Bousquet Mountain Ski Area
- Mohawk Mountain Ski Area
- Taconic State Park
- Ski Sundown
- Norman Rockwell Museum
- Naumkeag
- Berkshire Botanical Garden
- University of Connecticut
- Dcu Center
- Hancock Shaker Village
- Mount Holyoke College
- Mount Greylock
- Smith College
- Clark University
- Connecticut Science Center
- Xfinity Theatre




